1-Bromo-2-methylpropane → HCID 59559973, compound

HRID 1177084Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([OH:16])[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].Br[CH2:18][CH:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][CH2:18][CH:19]([CH3:21])[CH3:20])[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 4-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid methyl ester (3e) (167 mg, 0.75 mmol) in DMF (3 mL) was added 1-bromo-2-methylpropane (0.090 mL, 0.83 mmol) and cesium carbonate (520 mg, 1.6 mmol). The reaction mixture was stirred at 85° C. for 2 hr and cooled to room temperature. The mixture was quenched with H2O (10 mL), extracted with EtOAc (2×10 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 5% EtOAc in hexanes to give colorless oil (193 mg, 92% yield). 1H NMR (400 MHz, CDCl3) δ 7.09 (s, 1 H) 7.05 (s, 1 H) 3.89 (s, 3 H) 3.80 (d, J=6.57 Hz, 2 H) 2.99 (s, 2 H) 2.02-2.16 (m, 1 H) 1.49 (s, 6 H) 1.04 (s, 3 H) 1.02 (s, 3 H); LCMS for C16H22O4 m/z 279.10 (M+H+).

Workup

temperaturecooled to room temperature
customThe mixture was quenched with H2O (10 mL)
extractionextracted with EtOAc (2×10 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by flash column chromatography
washeluting with 5% EtOAc in hexanes

Sources & evidence

ORD record: ord-8fc0975cd23549458b22ede53a5c1576
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842713B2

Reaction notes

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